Bromine → HCID 58101276, compound

HRID 237324Notes

Reaction equation

HRID 237324 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:22]Br>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([Br:22])[C:10](=[O:14])[CH:9]1[CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 58101296HCID 58101296, compound

Product 1

HCID 58101276HCID 58101276, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-benzyl-3-oxo-piperidine-1-carboxylic acid tert-butyl ester (25.9 g, 0.09 mol) in CHCl3 (200 mL) was added Br2 (15.8 g, 0.099 mol, dissolved into 80 mL of CHCl3) dropwise at 0° C. After the addition, the mixture was stirred at 25° C. for 2 hrs, and then it was filtered. The filtrate was washed with saturated NaHSO3 and brine, dried over Na2SO4 and concentrated under reduced pressure to afford crude 2-benzyl-4-bromo-3-oxo-piperidine-1-carboxylic acid tert-butyl ester (18 g) as brown oil, which was used directly in the next step.

Workup

  1. additionAfter the addition
  2. filtrationit was filtered
  3. washThe filtrate was washed with saturated NaHSO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-469ac246a0814fe99a5a5baaa36351ac
Source dataset
uspto-grants-2014_02
Patent number
US08642587B2

Reaction notes

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